Lack of Resonance in Vinyl Halides

Rarely Tested

Hypothetical resonance structure is invalid due to orthogonality of orbitals:

$$CH_2=CH-Cl\not\leftrightarrow CH_2^+ - CH=Cl^-$$

The Cl lone pair in an sp² orbital cannot overlap with the C=C π-system, so the –M effect is negligible and the C(sp²)–Cl bond remains strong.

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